Triethylamine → 1-isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere {1-isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl}methanol (2.00 g, 5.43 mmol, prepared as in Parts A-F of Example 9) was dissolved in dichloromethane (20 mL) and dimethylsulfoxide (10 mL). Triethylamine (2.27 mL, 16.3 mmol) was added and the solution was cooled to 0° C. Sulfur trioxide pyridine complex (2.60 g, 16.3 mmol) was then added in four portions and the solution was stirred at 0° C. for another 2 hours. The solution was then poured into saturated aqueous ammonium chloride (70 mL) and extracted with diethyl ether (3×80 mL). The organics were washed with water (2×30 mL) and brine (20 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 1.84 g of 1-isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridine-2-carbaldehyde as a yellow residue.

Provenance & Evidence